
Family-friendly holiday rentals in Gaiole in Chianti
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Quick stats about holiday rentals that are family-friendly in Gaiole in Chianti

Total holiday rentals
Explore 20 holiday rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti holiday rentals start at $262 NZD per night before taxes and fees

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Over 140 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Gaiole in Chianti holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Gaiole in Chianti rentals

4.7 Average rating
Gaiole in Chianti stays receive an average rating of 4.7 out of 5 from guests
Top-rated family-friendly rentals in Gaiole in Chianti
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available
4.97 out of 5 average rating, 308 reviews
Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!
4.93 out of 5 average rating, 294 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.
4.92 out of 5 average rating, 359 reviews
Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.
4.99 out of 5 average rating, 155 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
5.0 out of 5 average rating, 352 reviews
Charming estate with views. A/C in the bedrooms
The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.
4.86 out of 5 average rating, 296 reviews
Casa Martini in Historic Chianti
Apartment with garden and private parking in Gaiole in Chianti, a stone's throw from the historic center where you will find numerous bars, restaurants and the small supermarket (coop). The accommodation is ideal for holidays with animals because it has a fully fenced garden. Tourist tax is required (€2 per person per night for the first seven nights) minors under 14 years excluded (read the complete regulation on the website of the Municipality of Gaiole in Chianti)
4.88 out of 5 average rating, 153 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
Typical Tuscan country house
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.
4.99 out of 5 average rating, 432 reviews
Tower Penthouse in small castle near Florence
900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.
4.96 out of 5 average rating, 139 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
4.91 out of 5 average rating, 100 reviews
Comfort Apartment in the Chianti Vineyards
Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, a kitchenette, a double bedroom, a private bathroom with a shower, air conditioning.
4.93 out of 5 average rating, 455 reviewsPopular amenities for Gaiole in Chianti family-friendly rentals
Family-friendly home rentals with a hot tub

Villa Lolù with private heated swimming-pool
4.98 out of 5 average rating, 160 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
4.99 out of 5 average rating, 116 reviews
A Big Dream in a Little Tower.
4.95 out of 5 average rating, 221 reviews
Palazzo Monaci - Pool in the Crete Senesi
4.96 out of 5 average rating, 142 reviews
Domus Nannini - Loggia Salimbeni SPA
4.96 out of 5 average rating, 156 reviews
Luxury frescoed apartment in the historical center
4.97 out of 5 average rating, 116 reviews
Agriturismo La Villa - L'Olivo, Pool & Hot Tub
4.98 out of 5 average rating, 241 reviews
Torretta Apartment
4.96 out of 5 average rating, 129 reviewsFamily- and pet-friendly home rentals

Manor House - IlVillinoFarmhouse
4.93 out of 5 average rating, 256 reviews
Villa Capanna, Private Pool, Breathtaking Views
4.89 out of 5 average rating, 309 reviews
La Dimora del Luca
4.98 out of 5 average rating, 171 reviews
The Loggia
4.93 out of 5 average rating, 153 reviews
Romantic apartment in the Tuscan village
4.89 out of 5 average rating, 343 reviews
Typical Tuscan Country House WITH A/C
4.98 out of 5 average rating, 294 reviews
Borgo Ripostena – No. 9 Oil Mill
4.94 out of 5 average rating, 118 reviews
Suite in Castello di Valle
4.88 out of 5 average rating, 128 reviewsFamily-friendly home rentals with a pool

The Castle of Ferrano - Castle in Tuscany
4.99 out of 5 average rating, 227 reviews
Villa Le Miccine w/ Pool - Bello Fresco Unit for 2
4.94 out of 5 average rating, 109 reviews
La Vignaccia (Farmhouse) - villa w/private pool
4.96 out of 5 average rating, 102 reviews
Relaxation and charm in the Chianti hills
4.99 out of 5 average rating, 115 reviews
La Loggia. House with pool and stunning view
4.99 out of 5 average rating, 104 reviews
Sestuccia
4.99 out of 5 average rating, 76 reviews
Riecine Capanna 4
5.0 out of 5 average rating, 9 reviews
Villa Eroica
4.97 out of 5 average rating, 32 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce





